Azo-dyestuffs and process of making same



Patented Aug. 23, 1932 UNITED STATES PATENT oFF cE GERALD BONHTE, OF BASEL, SWITZERLAND, ASSIGNOR TO THE FIISM SOCIETY OF CHEMICAL INDUSTRY IN BASLE, OF BASEL, SWITZERLAND AZO-DYESTUFFS AND PROCESS OF MAKING SAME No Drawing. Application filed October 24, 1931, Serial No. 570,981, and in Switzerland November 15, 1930. p n

The present invention relates to the manufacture of new a-zo-dyestufis. It comprises the process of making these dyestuffs, as well as the new dyestuffs themselves.

According to this process Valuable new dyestufl's are made when an arylide of 2:3-hydroxynaphthoio acid of the general formula on Z wherein a in one case stands for a substituent from a group of substituents comprising alkyl and alkoxy, and in the other case for hydrogen or a substituent of the just defined group, is coupled with a diazotized 2-amino-1 1-diphenylether of the general formula to blue-red dyestuffs are produced. These tints are also obtained when the dyestufi' is produced on the fiber, and they are characterin which the ys, ws and .es have the above explainedsignifications. In organic solvents, such as chlorlnated aromat1c hydrocarbons,

eg. chlorobenzene'or chloronaphthalene they dissolve to yellow-red to blue-red solutions.

The components to be diazotized can be 5 obtained, for example, by reduction of the condensation products obtainable from compounds such as 2-nitro-l:4-dichlorobenzene, l-nitro-Q l-dichlorobenzene, 1: 2-dinitro-5 chlorobenzene, 2-nitro-1 l-dibromobenzene, 1:2-dichloro-4: 5-dinitrobenzene, or the like, with nucleal substitution products of Ewamplel 3 23.1 parts of l-chloro-2-amino-4-methyl- 1:1'-diphenylether arediazotized as usual, 1

and the product is introduced into a solution of 27 .7 parts of 2: 3-hydroxynaphthoic a-cid-ortho-toluidide, 60 parts of caustic soda solution of 30 per cent. strengthand 15 parts of calcined'sodi-uni carbonate in 2,000 parts of water. The dyestufi is precipitated immediately. The red precipitate is filtered, washed and'dried.

I 7 Example 2 Cotton yarn is impregnate-d with a ground ing liquor made by dissolving 7 grams of ortho-anisidide of 2: 8-hydroxynaphthoic acid in 300 cc. of hot water with addition of 14 cc. of caustic soda solution of 30 per cent. strength and 10 cc. of Turkey red oil, the whole being diluted to 1 liter. then wound off and developed in a solution neutralized by means of sodium acetate containing 4 grams of diazotized 4: 4J-dichloro- 2-aminodiphenylether per liter. A red tint is produced which is of fastness. V

A scarlet-redshade is obtained with 4:: 2- dichloro-2-aminodiphenylether. I

In this example, 2: 3-hydroxynaphthoic acid--chloro-EZ-anisidide may be substituted The yarn is of excellent properties V 4:4-dichloramino-diphenylether The material to be printed is treated in the Foular d machine with an alkaline solution containing per liter 12 grams of the con densationproduct from 2z3-hydroxynaph thoic acid and 2,-aminohydroquinonedimethylether; When dry, the material is printed with a printing color, which-contains per kilo 8 grams of diazotized 4-chloro-2-amino- 4-methyl-1 1 -'diphenylether. pure red dyeing developsvery quickly and isremarkably fast.

The following table shows the shades of w some other dyestuffs which can be-made ac- The deep,

2. As new products the azo-dyestufi'sof the general formula h win in which of the five ys three stand; for hydrogen atoms, one fora substituent from a group of substituents consisting of alkyl, alkoxy and halogen, and one for a hydrogen atom or a substituent of the just defined group, and in which a in one cases stands for a substituent from a group of'substituents cording to the present lnvention 1-. V

4:4-dichloramino-diphenylethcr ortl1o-anisidide of 2:3-hydroxynaphthoic acid 7 Red 4:4- Do. para-phenetidlde of 2:3-l1ydroxynaphthoic acid Scarlet 4;4- Do. para-toluidide 0f 2:3-hydroxynaphthoic acid Do. I 4:2- D0. Do. Yellow scarlet 4-,2'- D0. v para-phenet dide of 2:3-hydroxynaphthoic acid, Scarlet 4-0111oro4-methoxy-2-amino-dipheny1ether ortho-anisidide oi 2:3-l1ydroxynaphtl10ic acid Blue-red Do; I para-anlsldide of 2:3-hydroxynaphthoic acid Bluish-red Do. 4-ch1oro-4-ethoxy-2-amino-diphenylether 4-chloro-4-metl1yl-2-amino-diphenylether 4-ch10ro-4-Inethyl-2-amino-diphenylether If these dyestuffs are to be produced on wool it is advantageous to work according to the particulars of British Patent No. 310,7 58.

What I claim is:

1. As new products the azo-dyestufis of the general formula case for a substituent of the just defined group or for ahydrogen atom, which products are red to dark red powders, dissolve ,iniliquid chlorinated aromatic hydrocarbons to red solutions, andyield vividscarlet red to blue red tints when produced on :the fibre, which combine purity with an excellent fastness to chlorine, keir-boiling and light.

para-phenetidide of 2:3-hydroxynaphthoio acid Do Do: Red

consisting of'alkyl and alkoxy, and in other case for a substituent of the justde fined group or for a hydrogen atom,'which products are red to dark red powders, dissolve in liquid chlorinated aromatic'hydrocarbons to red solutions, and yield vivid scarlet red to blue red tintswhen produced on the fibre, which combine purity with an excellent fastness to chlorine, keir-boiling and light. 7 p v 3. As new products theazo-dyestufi's of the general formula V I] a N in which of the two ys one stands for-a substituent from a' group of substituents uent from a group of substituents con sisting of alkyl and alkoxy, and in the other case for a substituentof the just defined group or for a hydrogen, atom, which products are red to dark red powders, dissolve in liquid chlorinated aromatic hydrocarbons to red solutions, and yield Vivid scarlet red to blue red tints when produced on the fibre, which combine purity with an excellent fastness to chlorine, keir-boiling and light.

4. As a new product the azo-dyestuff of the formula Ol-OOOCI which product is a red powder, dissolves in chlorobenzene to a red solution, and yields, when produced on the fibre, vivid pure red tints of an excellent fastness to chlorine, keir-boiling and light.

5. As new products the azo-dyestufls of the general formula in which of the two ys one stands for a subto blue red tints when produced on the fibre,

which combine purity with an excellent fastness to chlorine, keir-boiling and light.

6. As a new product the azo-dyestufl' of the formula which product is a red powder, dissolves in chlorobenzene to a scarlet red solution, and yields, when produced on the fibre, vivid pure scarlet red tints of an excellent fastness to chlorine, keir-boiling and light.

7. As a new product the'azo-dyes'tufi of the formula oHr-o-O-oOm which product is a red powder, dissolves in chlorobenzene to a blue red solution, and

yields, when produced on the fibre, vivid pure blue red tints of an excellent fastness to chlorine, keir-boiling and light.

In witness whereof, I have hereunto signed my name this 17th day of October, 1931.

GERALD BONI-IOTE. 

